Flight Routes from Tampa to Chicago Midway

Compare cheap outbound and return flights from Tampa (TPA) to Chicago Midway (MDW) and find the best offer from numerous airlines and travel agencies.

Trip type
Fastest flight
non-stop flights
81x / week
Flight distance
1,609 km
Time difference

Flight schedule from Tampa (TPA) to Chicago Midway (MDW)

Select a travel date in the flight schedule for the route from Tampa (TPA) to Chicago Midway (MDW) and compare affordable flight deals.

offers
Active filtersnone
Matching outbound flightsTPA–MDW · 14 of 14
fromto
dep.arr.
durationstopovers
  1. September 13 – 19, 2026
  2. September 20 – 26, 2026
  3. Sep 27 – Oct 3, 2026
    1. TPAMDW
      nonstop
      1. Southwest Airlines
    2. TPAMDW
      nonstop
      1. Southwest Airlines
    3. TPAMDW
      nonstop
      1. Southwest Airlines
    4. TPAMDW
      nonstop
      1. Southwest Airlines
    5. TPAMDW
      nonstop
      1. Southwest Airlines
    6. TPAMDW
      nonstop
      1. Southwest Airlines
    7. TPAMDW
      nonstop
      1. Southwest Airlines
    8. TPAMDW
      nonstop
      1. Southwest Airlines
    9. TPAMDW
      nonstop
      1. Southwest Airlines
    10. TPAMDW
      nonstop
      1. Southwest Airlines
    11. TPAMDW
      nonstop
      1. Southwest Airlines
    12. TPAMDW
      nonstop
      1. Southwest Airlines
    13. TPAMDW
      nonstop
      1. Southwest Airlines
    14. TPAMDW
      nonstop
      1. Southwest Airlines

      Tips and tricks to help you find cheap flights from Tampa to Chicago Midway

      Favorite airline: Frontier Airlines
      The most popular airline for flights from Tampa to Chicago Midway is Frontier Airlines.
      Frontier Airlines
      78 %
      Delta
      22 %
      Direct flights are cheaper
      Compared to direct flights, flights with a stopover on this route are on average 49 % more expensive.
      non stop flight
      1 stop
      02h 42min
      10h 15min
      $71
      $138
      The favorite connection is non-stop
      Flights from Tampa to Chicago Midway are most often booked as a direct flight.
      Route
      bookings
      Direct flights
      02h 42min, from $71
      50 %
      1 stopover Hartsfield-Jackson Atlanta International Airport, GA
      06h 30min, from $249
      27 %
      1 stopover Dallas-Fort Worth International Airport, T
      13h 23min, from $141
      18 %

      Important flight information

      Discover more flights around Tampa and Chicago Midway

      Departure airport Airport Tampa International Airport, FL (TPA)
      Arrival airport Airport Chicago Midway International Airport, IL (MDW)
      Destination country Flights to United States
      Departure airport - Destination country Tampa International Airport, FL - United States
      Departure airport - City-Code Tampa International Airport, FL - Chicago
      Alternative routes to United States
      Alternative flights to Chicago Midway